The glycosciences
Prof. Anja Hoffmann-Röder, Ludwig-Maximilians Universität München
This Thematic Series is a collection of Review articles summarizing the latest research results in the field of glycosciences, one of the most important areas of research in synthetic organic chemistry and biochemistry.
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Silyl-protective groups influencing the reactivity and selectivity in glycosylations
- Mikael Bols and
- Christian Marcus Pedersen
Beilstein J. Org. Chem. 2017, 13, 93–105, doi:10.3762/bjoc.13.12
Graphical Abstract
Figure 1: Silicon-protective groups typically used in carbohydrate chemistry.
Scheme 1: Glycosylation with sulfoxide 1.
Scheme 2: Glycosylation with imidate 4.
Scheme 3: Glycosylation with thioglycoside 7.
Scheme 4: In situ formation of a silylated lactosyl iodide for the synthesis of α-lactosylceramide.
Figure 2: Comparison of the reactivity of glycosyl donors with the pKa of the corresponding piperidinium ions....
Figure 3: Conformational change induced by bulky vicinal protective groups such as TBS, TIPS and TBDPS. The v...
Scheme 5: An example of a “one pot one addition” glycosylation, where 3 glucosyl donors are mixed with 2.1 eq...
Scheme 6: Superarmed-armed glycosylation with thioglycoside 34.
Scheme 7: One-pot double glycosylation with the conformationally armed thioglycoside 37.
Scheme 8: Superarmed-armed glycosylation with thioglycoside 41.
Figure 4: Donors disarmed by the di-tert-butylsilylene protective group.
Figure 5: The influence of a 3,6-O-tethering on anomeric reactivity and glycosylation selectivity. The α-thio...
Scheme 9: Regio- and stereoselective glycosylation using the superarmed thioglycoside donor 20.
Scheme 10: Superarmed donors used for C-arylation and the dependence of the size of the silylethers on the ste...
Scheme 11: β-Selective glucosylation with TIPS-protected glucosyl donors. The α-face is shielded by the bulky ...
Scheme 12: β-Selective rhamnosylation with a conformationally inverted donor.
Scheme 13: α-Selective galactosylation with DTBS-protected galactosyl donors.
Scheme 14: β-Selective arabinofuranosylation with a DTBS-protected donor.
Scheme 15: α-Selective glycosylation with a TIPDS-protected glucal donor.
Scheme 16: Highly β-selective glucuronylation using a 2,4-DTBS-tethered donor.
Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications
- Stephen Hill and
- M. Carmen Galan
Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67
Graphical Abstract
Scheme 1: Microwave-driven reaction of glucose in the presence of PEG-200 to afford blue-emissive CDs.
Scheme 2: Two-step synthesis of TTDDA-coated CDs generated from acid-refluxed glucose.
Scheme 3: Glucose-derived CDs using KH2PO4 as a dehydrating agent to both form and tune CD’s properties.
Scheme 4: Ultrasonic-mediated synthesis of glucose-derived CDs in the presence of ammonia.
Scheme 5: Tryptophan-derived CDs used for the sensing of peroxynitrite in serum-fortified cell media.
Scheme 6: Glucose-derived CDs conjugated with methotrexate for the treatment of H157 lung cancer cells.
Scheme 7: Boron-doped blue-emissive CDs used for sensing of Fe3+ ion in solution.
Scheme 8: N/S-doped CDs with aggregation-induced fluorescence turn-off to temperature and pH stimuli.
Scheme 9: N/P-doped hollow CDs for efficient drug delivery of doxorubicin.
Scheme 10: N/P-doped CDs applied to the sensing of Fe3+ ions in mammalian T24 cells.
Scheme 11: Comparative study of CDs formed from glucose and N-doped with TTDDA and dopamine.
Scheme 12: Formation of blue-emissive CDs from the microwave irradiation of glycerol, TTDDA and phosphate.
Scheme 13: Xylitol-derived N-doped CDs with excellent photostability demonstrating the importance of Cl incorp...
Scheme 14: Base-mediated synthesis of CDs with nanocrystalline cores, from fructose and maltose, without forci...
Scheme 15: N/P-doped green-emissive CDs working in tandem with hyaluronic acid-coated AuNPs to monitor hyaluro...
Scheme 16: Three-minute microwave synthesis of Cl/N-doped CDs from glucosamine hydrochloride and TTDDA to affo...
Scheme 17: Mechanism for the formation of N/Cl-doped CDs via key aldehyde and iminium intermediates, monitored...
Scheme 18: Phosphoric acid-mediated synthesis of orange-red emissive CDs from sucrose.
Scheme 19: Proposed HMF dimer, and its formation mechanism, that upon aggregations bestows orange-red emissive...
Scheme 20: Different polysaccharide-derived CDs in the presence of PEG-200 and how the starting material compo...
Scheme 21: Tetracycline release profiles for differentially-decorated CDs.
Scheme 22: Hyaluronic acid (HA) and glycine-derived CDs, suspected to be decorated in unreacted HA, allowing r...
Scheme 23: Cyclodextrin-derived CDs used for detection of Ag+ ions in solution, based on the formal reduction ...
Scheme 24: Cyclodextrin and OEI-derived CDs, coated with hyaluronic acid and DOX, to produce an effective lung...
Scheme 25: Cellulose and urea-derived N-doped CDs with green-emissive fluorescence.
Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience
- Serge Pérez and
- Daniele de Sanctis
Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114
Graphical Abstract
Figure 1: Complementarity of synchrotron radiation and neutron sources to investigate the structure of matter....
Figure 2: A representation of a synchrotron storage ring, including linear accelerator, booster and two beaml...
Figure 3: Schematic representation of a sector of a storage ring. Bending magnets and insertion devices are a...
Figure 4: Structural features of the resin glycoside tricolorin A. (a) Extracted from the Mexican variety of ...
Figure 5: Powder diffractogram measured on a synthetic pentasaccharide from heparin, at ESRF beamline ID31, λ...
Figure 6: Three dimensional ribbon representation of a heavily N-glycosylated Aspergilllus sp. Family GH3 β-D...
Figure 7: Histogram of the number of deposited crystal structures of glycan-binding proteins deposited over t...
Figure 8: Ribbon diagram representations of prototypical members of the GT-A and GT-B super-family fold, resp...
Figure 9: Representation of the FUT1 structure determined in complex with the acceptor (carbon atoms in green...
Figure 10: Representation of the seven folds most commonly found in glycoside hydrolases. From the classificat...
Figure 11: The multivalent carbohydrate binding features of lectins from X-ray structures. (a) Monovalent. E-s...
Figure 12: Three-dimensional depiction of the ternary complex formed by a heparin mimetic in interaction with ...
Figure 13: 3D representation of different sugar transporter structures: (left to right, top to down) lactose p...
Figure 14: Kinetic crystallography. Protein crystals are soaked with the cage compound (Step 1) followed by fl...
Figure 15: Reconstruction of the full three-dimensional structure of the soluble lectin (BC2L-C) from the oppo...
Figure 16: Characterization by synchrotron X-ray reflectometry of the transverse structures of a model membran...
Figure 17: Complementary use of X-ray synchrotron and neutron fiber diffraction to unravel the three-dimension...
Figure 18: Scanning electron micrograph of high-quality micrometer-sized A-amylose microcrystals grown from sh...
Figure 19: Cartography of distribution and orientation of cellulose in wood using a 3 µm X-ray beam. The scann...
Figure 20: Structural micro-diffraction scanning of a starch granule from Phajus grandifolius with dimensions ...
Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides
- Jihen Ati,
- Pierre Lafite and
- Richard Daniellou
Beilstein J. Org. Chem. 2017, 13, 1857–1865, doi:10.3762/bjoc.13.180
Graphical Abstract
Figure 1: Mechanisms of O-GTs-catalysed glycosylation.
Figure 2: Desulfoglucosinolate biosynthesis by UGT74B1.
Figure 3: Examples of thiol-containing acceptors used in the chemo-enzymatic biosynthesis of S-glycosides cat...
Figure 4: Examples of C-glycosylated products biosynthesized by natural C-GT. Compounds showed are formed by ...
Figure 5: General mechanisms of the O-GHs-catalysed hydrolysis.
Figure 6: Neighbouring group participation mechanism of retaining the O-GHs-catalysed hydrolysis.
Figure 7: Mechanism of the thioligases.
Figure 8: Examples of thiol acceptors utilized with GHs.
Intramolecular glycosylation
- Xiao G. Jia and
- Alexei V. Demchenko
Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201
Graphical Abstract
Scheme 1: The mechanistic outline of the intermolecular (a) and intramolecular (b) glycosylation reactions.
Figure 1: Three general concepts for intramolecular glycosylation reactions.
Scheme 2: First intramolecular glycosylation using the molecular clamping.
Scheme 3: Succinoyl as a flexible linker for intramolecular glycosylation of prearranged glycosides.
Scheme 4: Template-directed cyclo-glycosylation using a phthaloyl linker.
Scheme 5: Phthaloyl linker-mediated synthesis of branched oligosaccharides via remote glycosidation.
Scheme 6: Molecular clamping with the phthaloyl linker in the synthesis of α-cyclodextrin.
Scheme 7: m-Xylylene as a rigid tether for intramolecular glycosylation.
Scheme 8: Oligosaccharide synthesis using rigid xylylene linkers.
Scheme 9: Stereo- and regiochemical outcome of peptide-based linkers.
Scheme 10: Positioning effect of donor and acceptor in peptide templated synthesis.
Scheme 11: Synthesis of a trisaccharide using a non-symmetrical tether strategy.
Scheme 12: Effect of ring on glycosylation with a furanose.
Scheme 13: Rigid BPA template with various linkers.
Scheme 14: The templated synthesis of maltotriose in complete stereoselectivity.
Scheme 15: First examples of the IAD.
Scheme 16: Long range IAD via dimethylsilane.
Scheme 17: Allyl-mediated tethering strategy in the IAD.
Scheme 18: IAD using tethering via the 2-naphthylmethyl group.
Scheme 19: Origin of selectivity in boronic ester mediated IAD.
Scheme 20: Arylborinic acid approach to the synthesis of β-mannosides.
Figure 2: Facial selectivity during HAD.
Scheme 21: Possible mechanisms to explain α and β selectivity in palladium mediated IAD.
Scheme 22: DISAL as the leaving group that favors the intramolecular glycosylation pathway.
Scheme 23: Boronic acid as a directing group in the leaving group-based glycosylation method.
Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly
- Weizhun Yang,
- Bo Yang,
- Sherif Ramadan and
- Xuefei Huang
Beilstein J. Org. Chem. 2017, 13, 2094–2114, doi:10.3762/bjoc.13.207
Graphical Abstract
Scheme 1: a) Traditional glycosylation typically employs the premixed approach with both the donor and the ac...
Scheme 2: Glycosylation of an unreactive substrate. Reagents and conditions: (a) Tf2O, −78 °C, CH2Cl2 (DCM), ...
Scheme 3: Bromoglycoside-mediated glycosylation.
Scheme 4: Glycosyl bromide-mediated selenoglycosyl donor-based iterative glycosylation. Reagents and conditio...
Scheme 5: Preactivation-based glycosylation using 2-pyridyl glycosyl donors.
Scheme 6: Chemoselective dehydrative glycosylation. Reagents and conditions: (a) Ph2SO, Tf2O, 2-chloropyridin...
Figure 1: Representative structures of products formed by the preactivation-based dehydrative glycosylation o...
Scheme 7: Possible mechanism for the dehydrative glycosylation. (a) Formation of diphenyl sulfide bis(triflat...
Scheme 8: Chemoselective iterative dehydrative glycosylation. Reagents and conditions: (a) Ph2SO, Tf2O, 2,4,6...
Scheme 9: Chemoselective iterative dehydrative glycosylation. Reagents and conditions: (a) Ph2SO, Tf2O, −40 °...
Scheme 10: Chemical synthesis of a hyaluronic acid (HA) trimer 47. Reagents and conditions: (a) Ph2SO, TTBP, CH...
Figure 2: Retrosynthetic analysis of pentasaccharide 48.
Scheme 11: Effects of anomeric leaving groups on glycosylation outcomes. Reagents and conditions: (a) Ph2SO, Tf...
Scheme 12: Reactivity-based one-pot chemoselective glycosylation.
Scheme 13: Preactivation-based iterative glycosylation of thioglycosides.
Scheme 14: BSP/Tf2O promoted synthesis of 75.
Scheme 15: Proposed mechanism for preactivation-based glycosylation strategy.
Figure 3: The preactivations of glycosyl donors 83, 85 and 87 were investigated by low temperature NMR, which...
Scheme 16: The more electron-rich glycosyl donor 91 gave a higher glycosylation yield than the glycosyl donor ...
Scheme 17: Comparison of the BSP/Tf2O and p-TolSCl/AgOTf promoter systems in facilitating the preactivation-ba...
Scheme 18: One-pot synthesis of Globo-H hexasaccharide 105 using building blocks 101, 102, 103 and 104.
Scheme 19: Synthesis of (a) oligosaccharides 109–113 towards (b) 30-mer galactan 115. Reagents and conditions:...
Figure 4: Structure of mycobacterial arabinogalactan 116.
Figure 5: Representative complex glycans from glycolipid family synthesized by the preactivation-based thiogl...
Figure 6: Representative microbial and mammalian oligosaccharides synthesized by the preactivation-based thio...
Figure 7: Some representative mammalian oligosaccharides synthesized by the preactivation-based thioglycoside...
Figure 8: Preparation of a heparan sulfate oligosaccharides library.
Scheme 20: Synthesis of oligo-glucosamines through electrochemical promoted preactivation-based thioglycoside ...
Scheme 21: Synthesis of 2-deoxyglucosides through preactivation. Reagents and conditions: a) AgOTf, p-TolSCl, ...
Scheme 22: Synthesis of tetrasaccharide 153. Reagents and conditions: (a) AgOTf, p-TolSCl, CH2Cl2, −78 °C; the...
Scheme 23: Aglycon transfer from a thioglycosyl acceptor to an activated donor can occur during preactivation-...
What contributes to an effective mannose recognition domain?
- Christoph P. Sager,
- Deniz Eriş,
- Martin Smieško,
- Rachel Hevey and
- Beat Ernst
Beilstein J. Org. Chem. 2017, 13, 2584–2595, doi:10.3762/bjoc.13.255
Graphical Abstract
Figure 1: CRDs of the analyzed crystal structures, with mannose pyranosyl units similarly aligned in each str...
Figure 2: A) The solvent exposed binding site of E-selectin interacting with sLex (PDB: 1G1T) [53]. B) The buried...
Figure 3: Dynamic mannose–receptor interactions (20 ns MD simulations), grouped according to the nature of th...
Figure 4: Desolvation of hydroxy groups. A) The desolvation cost of a single hydroxy group associated with th...
Figure 5: Model view of the binding site interactions of DC-SIGN (E) and BC2L-A (H) with water. A) The solven...
Figure 6: Thermodynamic fingerprints of sLex bound to E-selectin and n-heptyl α-D-mannoside bound to FimHLD (I...
Figure 7: Schematic overview of the conformational changes of FimH (I). FimH crystal structures, which corres...
Figure 8: Comparison of the holo (white) and apo (green, magenta) binding sites of LecB (G) and BDCA-2 (A), r...
Recent applications of click chemistry for the functionalization of gold nanoparticles and their conversion to glyco-gold nanoparticles
- Vivek Poonthiyil,
- Thisbe K. Lindhorst,
- Vladimir B. Golovko and
- Antony J. Fairbanks
Beilstein J. Org. Chem. 2018, 14, 11–24, doi:10.3762/bjoc.14.2
Graphical Abstract
Figure 1: The three major methods for the synthesis of GAuNPs. (a) Direct reduction of an Au3+ salt in the pr...
Scheme 1: The non-catalysed azide–alkyne Huisgen cycloaddition (NCAAC) between an organic azide (1,3-dipole) ...
Scheme 2: Ligand exchange and NCAAC on an AuNP surface. Reagents and conditions: (a) Br(CH2)11SH in DCM, 60 h...
Scheme 3: Azide functionalization and NCAAC on an AuNP surface using electron deficient alkynes. Reagents and...
Scheme 4: NCAAC performed under hyperbaric conditions. Reagents and conditions: (a) Br(CH2)11SH in C6H6, 48 h...
Scheme 5: The synthesis of AuNPs functionalized with strained alkyne derivatives. HBTU = O-benzotriazole-N,N,N...
Scheme 6: A schematic representation of the SPAAC between azide-functionalized polymersomes and strained alky...
Scheme 7: Functionalization of AuNPs with an azide containing thiol ligand, and subsequent attachment to an a...
Scheme 8: Surface modification of AuNPs using microwave-assisted CuAAC. Reagents and conditions: (a) HS(CH2)11...
Scheme 9: AuNP functionalization and efficient CuAAC with a range of alkynes reported by Boisselier et al. [62]. ...
Scheme 10: Schematic illustration of: (a) AuNP deposition on a carbon electrode; (b) formation of alkyne-termi...
Scheme 11: (a) Synthesis of the alkyne-terminated thiol (ATT) ligand 33; (b) synthesis of 12 nm sized ATT-AuNP...
Scheme 12: Synthesis of (a) cyclooctyne-functionalized AuNPs and (b) GAuNPs using SPAAC [82].
Aminosugar-based immunomodulator lipid A: synthetic approaches
- Alla Zamyatina
Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3
Graphical Abstract
Figure 1: (A) Gram-negative bacterial membrane with LPS as major component of the outer membrane; (B) structu...
Figure 2: Structures of representative TLR4 ligands: TLR4 agonists (E. coli lipid A, N. meningitidis lipid A ...
Figure 3: (A) Co-crystal structure of the homodimeric E. coli Ra-LPS·hMD-2∙TLR4 complex (PDB code: 3FXI); (B)...
Figure 4: Co-crystal structures of (A) hybrid TLR4·hMD-2 with the bound antagonist eritoran (PDB: 2Z65, TLR4 ...
Scheme 1: Synthesis of E. coli and S. typhimurium lipid A and analogues with shorter acyl chains.
Scheme 2: Synthesis of N. meningitidis Kdo-lipid A.
Scheme 3: Synthesis of fluorescently labeled E. coli lipid A.
Scheme 4: Synthesis of H. pylori lipid A and Kdo-lipid A.
Scheme 5: Synthesis of tetraacylated lipid A corresponding to P. gingivalis LPS.
Scheme 6: Synthesis of pentaacylated P. gingivalis lipid A.
Scheme 7: Synthesis of monophosphoryl lipid A (MPLA) and analogues.
Scheme 8: Synthesis of tetraacylated Rhizobium lipid A containing aminogluconate moiety.
Scheme 9: Synthesis of pentaacylated Rhizobium lipid A and its analogue containing ether chain.
Scheme 10: Synthesis of pentaacylated Rhizobium lipid A containing 27-hydroxyoctacosanoate lipid chain.
Scheme 11: Synthesis of zwitterionic 1,1′-glycosyl phosphodiester: a partial structure of GalN-modified Franci...
Scheme 12: Synthesis of a binary 1,1′-glycosyl phosphodiester: a partial structure of β-L-Ara4N-modified Burkh...
Scheme 13: Synthesis of Burkholderia lipid A containing binary glycosyl phosphodiester linked β-L-Ara4N.
Synthetic and semi-synthetic approaches to unprotected N-glycan oxazolines
- Antony J. Fairbanks
Beilstein J. Org. Chem. 2018, 14, 416–429, doi:10.3762/bjoc.14.30
Graphical Abstract
Scheme 1: The first ENGase-catalysed glycosylation of a GlcNAc acceptor using an N-glycan oxazoline as donor.
Scheme 2: Production of N-glycan oxazolines from peracetylated sugars using Lewis acids.
Scheme 3: Direct conversion of unprotected GlcNAc to a glycosyl oxazoline by treatment with DMC and Et3N in w...
Scheme 4: Total synthesis of a truncated complex biantennary N-glycan oxazoline via an epimerisation approach...
Scheme 5: Wangs’s total synthesis of an N-glycan oxazoline incorporating click handles, employing Crich direc...
Scheme 6: Wangs’s total synthesis of an N-glycan dodecasaccharide oxazoline employing final step oxazoline fo...
Scheme 7: Production of a phosphorylated N-glycan oxazoline, employing final step oxazoline formation with DM...
Scheme 8: Enzymatic degradation of locust bean gum, and chemical conversion into an N-glycan dodecasaccharide...
Scheme 9: Production of a complex biantennary N-glycan oxazoline from hens’ eggs by semi-synthesis via isolat...
Scheme 10: Production of a high mannose (Man-9) N-glycan oxazoline from soy bean flour.
Scheme 11: Production of a triantennary N-glycan oxazoline from bovine feruin by semi-synthesis.
Carbohydrate inhibitors of cholera toxin
- Vajinder Kumar and
- W. Bruce Turnbull
Beilstein J. Org. Chem. 2018, 14, 484–498, doi:10.3762/bjoc.14.34
Graphical Abstract
Figure 1: a) Ribbon and b) surface depictions of the cholera toxin: A11 domain in light blue; A12 domain in d...
Figure 2: a) Structure of the cholera toxin showing the location of its carbohydrate binding sites and the st...
Figure 3: Bernardi and co-workers’ designed oligosaccharide mimetics of GM1.
Figure 4: Structure of monomeric ligands. X = amino acid residues, aminoalkyl, 1,2,3 triazoles; n = 1, 2; R =...
Figure 5: Bivalent inhibitor designed and synthesised by Pickens et al.
Figure 6: Bivalent inhibitor designed and synthesized by Arosio et al.
Figure 7: Bivalent inhibitors designed and synthesised by Leaver and Liu.
Figure 8: Bivalent and tetravalent inhibitor designed and synthesised by Pieters, and Bernardi et al.
Figure 9: Cyclic inhibitors synthesised by Kumar et al. for CT.
Figure 10: The star-shaped inhibitors reported by Fan, Hol and co-workers.
Figure 11: Differently sized cyclic decavalent peptide core designed by Zhang et al.
Figure 12: Calix[5]arene core-based pentavalent inhibitor designed by Garcia-Hartjes et al.
Figure 13: Corannulene core-based pentavalent inhibitor designed by Mattarella et al.
Figure 14: Pentavalent inhibitor designed by Pieters and co-workers.
Figure 15: Neoglycoprotein inhibitor based on a non-binding mutant of CTB.
Figure 16: Octavalent inhibitor designed by Pieters, Bernardi and co-workers.
Figure 17: Hetero-bifunctional inhibitor designed by Bundle and co-workers.
Figure 18: Glycopolymers with exchangeable sugar ligands and variable length linkers.
Anomeric modification of carbohydrates using the Mitsunobu reaction
- Julia Hain,
- Patrick Rollin,
- Werner Klaffke and
- Thisbe K. Lindhorst
Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138
Graphical Abstract
Scheme 1: Left: The Mitsunobu reaction is essentially a nucleophilic substitution of alcohols occurring with ...
Scheme 2: Mechanistic considerations on the Mitsunobu reaction with carbohydrate hemiacetals (depicted in sim...
Scheme 3: Anomeric esterification using the Mitsunobu procedure [29].
Scheme 4: Conversion of allyl glucuronate into various 1-O-esterified allyl glucuronates using anomeric Mitsu...
Scheme 5: Synthesis of anomeric glycosyl esters as substrates for Au-catalyzed glycosylation [40].
Scheme 6: Correlation between pKa value of the employed acids (or alcohol) and the favoured anomeric configur...
Scheme 7: Synthesis of the β-mannosyl phosphates for the synthesis of HBP 43 by anomeric phosphorylation acco...
Scheme 8: Synthesis of phenyl glycosides 44 and 45 from unprotected sugars [24].
Scheme 9: Synthesis of azobenzene mannosides 47 and 48 without protecting group chemistry [46].
Scheme 10: Synthesis of various aryl sialosides using Mitsunobu glycosylation [25].
Scheme 11: Mitsunobu synthesis of different jadomycins [54,55]. BOM: benzyloxymethyl.
Scheme 12: Stereoselectivity in the Mitsunobu synthesis of catechol glycosides in the gluco- and manno-series [56]....
Scheme 13: Formation of a 1,2-cis glycoside 80 assisted by steric hindrance of the β-face of the disaccharide ...
Scheme 14: Stereoselective β-D-mannoside synthesis [60].
Scheme 15: TIPS-assisted synthesis of 1,2-cis arabinofuranosides [63]. TIPS: triisopropylsilyl.
Scheme 16: The Mitsunobu reaction with glycals leads to interesting rearrangement products [69].
Scheme 17: Synthesis of disaccharides using mercury(II) bromide as co-activator in the Mitsunobu reaction [75].
Scheme 18: Synthesis of various fructofuranosides according to Mitsunobu and proposed neighbouring group parti...
Scheme 19: The Mitsunobu reaction allows stereoslective acetalization of dihydroartemisinin [77].
Scheme 20: Synthesis of alkyl thioglycosides by Mitsunobu reaction [81].
Scheme 21: Preparation of iminoglycosylphthalimide 115 from 114 [85].
Scheme 22: Mitsunobu reaction as a key step in the total synthesis of aurantoside G [87].
Scheme 23: Utilization of an N–H acid in the Mitsunobu reaction [88].
Scheme 24: Mitsunobu reaction with 1H-tetrazole [89].
Scheme 25: Formation of a rebeccamycin analogue using the Mitsunobu reaction [101].
Scheme 26: Synthesis of carbohydrates with an alkoxyamine bond [114].
Scheme 27: Synthesis of glycosyl fluorides and glycosyl azides according to Mitsunobu [118,119].
Scheme 28: Anomeric oxidation under Mitsunobu conditions [122].
Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections
- Matthew B. Calvert,
- Varsha R. Jumde and
- Alexander Titz
Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239
Graphical Abstract
Figure 1: Mannosides as inhibitors of the lectin FimH from uropathogenic Escherichia coli.
Figure 2: Galactosides targeting uropathogenic Escherichia coli FmlH (compounds 8 and 9) and Pseudomonas aeru...
Figure 3: Mannosides and fucosides as inhibitors of P. aeruginosa LecB.
Figure 4: β-Cyclodextrin-based antitoxin 19 against S. aureus α-hemolysin and the decavalent Shiga toxin inhi...
Figure 5: The mechanism of quorum sensing and representative signaling molecules.
Figure 6: Inhibitors of bacterial quorum sensing.
Lectins of Mycobacterium tuberculosis – rarely studied proteins
- Katharina Kolbe,
- Sri Kumar Veleti,
- Norbert Reiling and
- Thisbe K. Lindhorst
Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1
Graphical Abstract
Figure 1: Immune cells (e.g., macrophages) and epithelial cells express lectins on the cell surface (e.g., de...
Figure 2: Both mycobacteria and mammalian host cells possess unique subsets of glycosides on their cell surfa...
Figure 3: Structure of FimH CRD with a docked azobenzene mannobioside showing the aromatic aglycon and the ty...
Figure 4: Computer-based genome analysis supports the existence of mycobacterial glycan-binding proteins, whi...
Figure 5: Amino acid sequence and secondary structure alignments of Mtb proteins encoded by Rv1419 and Rv2075...
Figure 6: Recently, pili were detected on the cell surface of Mtb, which were classified as curli and type IV...
